Has Andrew Mason Announced His Next Move?

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By this point, it’s ancient news that Andrew Mason was fired from Groupon, the company he founded. It happened late last week, and the move already has been analyzed to death even though it was a long time coming to even those who loosely follow the news.

What’s more exciting to speculate over is where Mason will go from here. Hopefully he’ll have learned his lesson not to be steamrolled over by his own success to expand too quickly. That’s part of what did Mason in, and perhaps Groupon eventually (we’ll see), but Mason obviously has always been an ideas guy. Groupon wasn’t his first idea and certainly won’t be his last.

His Twitter has grown increasingly quiet since the axe fell, but there’s a tweet a few weeks back that may indicate where Mason’s mind is and how he might set things into motion for his next business venture.

I, of course, am speculating. Wildly. But let’s get into it.

Check this out: On February 24, he hypothetically asked the world, “Possible to write a gmail script to autoreply & bounce emails longer than fifty words?”

So, is it possible Mason might be kicking around ways to improve the online email experience? Not specific to Gmail, per se, although there would be a satisfying irony in that if they snatch him up, given that Google tried to buy Groupon in 2010. It’s possible I’m grasping at straws, but Mason has been increasingly tweeting about services and products he’s frustrated by — like a few weeks ago when he griped about restaurants that serve mayo even when you don’t ask for it. But that, combined with the fact he elected to take a second job at an undisclosed Japanese restaurant in Wicker Park, could be a predictor of what’s next.

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. His first career aspirations were to be a game-show host.

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